If so, what would that look like?

This sounds like a solid long-term plan!

 @Casey Ram I can tell the followings that I feel like they are the important bits. 

Take ownership of your mistake and learn to do the proper due diligence recommended above😊https://www.biggerpockets.com/member-blogs/3094/91097-why-you-should-screen-a-pm-company-like-you-screen-for-tenantshttps://www.biggerpockets.com/member-blogs/3094/91878-how-to-screen-a-pmc-better-than-a-tenant-part-2-communication-and-documhttps://www.biggerpockets.com/member-blogs/3094/91879-how-to-screen-a-pmc-better-than-a-tenant-part-3-the-management-contr

Hey @Fara Heath, welcome to the BP Forum and this sounds like an awesome opportunity!

I don't know how active your where with your HOA, like attending the meetings, but the community should have been informed about the insurance way before the change took effect.

Quote from @Kerri Forrest: My real estate strategy includes (potentially) purchasing a condo in Washington, DC to rent until I'm in a position to move back there BUT it feels like the condo market is under siege right now.

DM us if you’d like to discuss this logical approach in greater detail!

Ideally I would like to have at least 1 LTR, 1 STR and then flip 1-2 houses a year. 

Quote from @NA Newman: Hi, are there softwares that find underpriced properties, or good potential deals for specific locations (like zip code or city)?